2,4-Dichloro-D-Phenylalanine is a non-proteinogenic, halogenated phenylalanine derivative featuring a D-configuration at the α-carbon and a benzyl side chain bearing two chlorine substituents at the 2- and 4-positions. The molecule contains both an α-amino group and a carboxylic acid functional group, with the electron-withdrawing dichloro substitution on the aromatic ring modulating side-chain polarity, hydrogen-bonding patterns, and aromatic reactivity relative to unsubstituted phenylalanine. As a chemically defined amino acid analogue, it is used in peptide and structure-activity studies where altered aromatic substitution and stereochemistry are required, and it can serve as a substrate or building block for preparing halogenated peptide derivatives for analytical method development and chemical biology experiments involving labeled or modified amino acid side chains.
CAT No: CP12102
CAS No:114872-98-9
Synonyms/Alias:2,4-Dichloro-D-phenylalanine;114872-98-9;D-2,4-Dichlorophenylalanine;(2R)-2-amino-3-(2,4-dichlorophenyl)propanoicacid;(R)-2-AMINO-3-(2,4-DICHLOROPHENYL)PROPANOICACID;D-2,4-DICHLOROPHE;AC1ODU3I;(2R)-2-Amino-3-(2,4-dichlorophenyl)propionicacid;2(3H)-Furanone,dihydro-3,5-dimethyl-5-[2-(1-oxopropoxy)ethyl]-;SCHEMBL1613174;CTK4A8950;D-PHE(2,4-DICL)-OH;MolPort-001-758-765;H-D-PHE(2,4-DICL)-OH;H-D-PHE(2,4-CL2)-OH;ZINC1653228;ANW-51973;MFCD01860873;AKOS012010401;AKOS015850049;AB10084;AC-5847;AM82014;CS13525;DS-0451
2,4-Dichloro-D-Phenylalanine is a halogenated, D-configured phenylalanine analog featuring two chlorine substituents on the aromatic ring. This non-proteinogenic amino acid building block is used in medicinal chemistry and chemical biology workflows where aryl halogenation is employed to tune physicochemical properties and support structure-activity relationship (SAR) studies. Its defined stereochemistry and aromatic substitution pattern make it a practical component for preparing halogen-rich peptide mimetics and related intermediates for downstream synthesis.
1. Peptidomimetic Building Blocks
2,4-Dichloro-D-Phenylalanine is used as a D-amino acid building block for constructing peptidomimetic scaffolds and modified peptide analogs in custom synthesis and research-grade lead optimization. The dichloro-substituted phenyl side chain provides a chemically robust aromatic motif that is frequently leveraged to probe how steric and electronic effects influence binding-site interactions in SAR campaigns. Medicinal chemistry groups and peptide research laboratories commonly incorporate this type of D-configured, halogenated residue into solution-phase or solid-phase assembly strategies to generate stereochemically defined analog libraries for structure-property evaluation.
2. Medicinal Chemistry SAR Intermediates
2,4-Dichloro-D-Phenylalanine serves as a practical intermediate for medicinal chemistry programs that require halogenated amino acid fragments. The presence of two aryl chlorine atoms supports the preparation of analog series where lipophilicity, aromatic electronics, and conformational preferences are systematically varied while maintaining a consistent stereochemical center. Pharmaceutical intermediate development teams use this building block to streamline the synthesis of candidate-related compounds, including side-chain-modified derivatives and stereochemically controlled analogs used in hit-to-lead refinement and lead optimization workflows.
3. Chemical Biology Probe Synthesis
2,4-Dichloro-D-Phenylalanine is applied in chemical biology for the synthesis of halogenated amino acid probes and tagged analogs used to interrogate binding interactions and residue-specific recognition in vitro. Laboratories developing small-molecule or peptide-based probes often select halogenated aromatic residues to improve synthetic handle stability and to create defined aromatic environments for interaction studies. When downstream workflows require a D-stereochemical element to modulate recognition or proteolytic handling in assay contexts, this building block provides a consistent, stereodefined platform for probe construction and subsequent functionalization.
4. Analytical Reference Standards
2,4-Dichloro-D-Phenylalanine is used as a defined chemical reference in analytical method development and characterization studies involving halogenated amino acid motifs. Analytical laboratories employ such stereochemically defined standards to support LC-MS identification, retention-time matching, and method qualification for compounds containing dichloro-phenylalanine-like fragments. This use is particularly relevant in impurity profiling, reaction monitoring, and intermediate characterization during pharmaceutical intermediate synthesis, where unambiguous reference material improves data interpretation for halogenated aromatic analytes.
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